Which NHL team has gone the longest without a Stanley Cup? With a first-round exit in the 2022 playoffs, the Maple Leafs tied the record for longest Stanley Cup drought in NHL history, matching the New York Rangers’ mark from 1940 to 1994. After the Maple Leafs, the Buffalo Sabres and Vancouver Canucks share the second-longest Cup drought at 51 years.
What two years did they not have a champion in the NHL? The Montreal Canadiens have won the Stanley Cup 24 times and made the Finals an additional eleven times. There were two years when the Stanley Cup was not awarded: 1919, because of the Spanish flu pandemic, and 2005, because of the NHL lockout.
Has any team won 3 Stanley Cups in a row? Toronto Maple Leafs (1962, 1963)
The Toronto Maple Leafs won three straight Stanley Cups between 1962 and ’64, and the ’63 team was their best.
Has any team won 5 Stanley Cups in a row? On April 14, 1960, the Montreal Canadiens defeat the Toronto Maple Leafs to win the Stanley Cup for a record fifth year in a row.